(2S,3S,4R,5S)-1-benzyloxycarbonyl-2-carboxy-5-methylpyrrolidine-3,4-diol

Base Information

• Chemical Name: (2S,3S,4R,5S)-1-benzyloxycarbonyl-2-carboxy-5-methylpyrrolidine-3,4-diol
• CAS No.: 869857-96-5
• Molecular Formula: C₁₇H₂₁NO₆
• Molecular Weight: 335.357
• Mol file: 869857-96-5.mol

Synonyms:(2S,3S,4R,5S)-1-benzyloxycarbonyl-2-carboxy-5-methylpyrrolidine-3,4-diol

Chemical Property of (2S,3S,4R,5S)-1-benzyloxycarbonyl-2-carboxy-5-methylpyrrolidine-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5S)-1-benzyloxycarbonyl-2-carboxy-5-methylpyrrolidine-3,4-diol

There total 9 articles about (2S,3S,4R,5S)-1-benzyloxycarbonyl-2-carboxy-5-methylpyrrolidine-3,4-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

(2S,3S,4R,5S)-1-benzyloxycarbonyl-2-formyl-5-methylpyrrolidine-3,4-diol (869857-92-1) → (2S,3S,4R,5S)-1-benzyloxycarbonyl-2-carboxy-5-methylpyrrolidine-3,4-diol (869857-96-5)

Guidance literature:

With sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene; In tert-butyl alcohol; at 20 ℃;

DOI:10.1039/b508855k

Reference yield: 75.0%

C19H26O6 → (2S,3S,4R,5S)-1-benzyloxycarbonyl-2-carboxy-5-methylpyrrolidine-3,4-diol (869857-96-5)

Guidance literature:

C₁₉H₂₆O₆; With sodium periodate; In tetrahydrofuran; water;

With sodium chlorite; potassium dihydrogenphosphate; In water; tert-butyl alcohol;

DOI:10.1002/ejoc.201300878

Reference yield:

1-{(4R,5S)-5-[(R)-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol → (2S,3S,4R,5S)-1-benzyloxycarbonyl-2-carboxy-5-methylpyrrolidine-3,4-diol (869857-96-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 74 percent / pyridine; DMAP

2: 55 percent / trimethylsilyl azide; tetrabutylammonium fluoride / dimethylformamide / 4.5 h / 90 °C

3: H₂ / Pd/C / methanol / 2 h / atmospheric pressure

4: 265 mg / DBU / methanol / 12 h / 20 °C

5: aq. NaHCO₃ / ethanol / 2 h / 20 °C

6: 0.966 g / aq. Zn(NO₃)2 / acetonitrile / 12 h / 50 °C

7: 92 percent / aq. NaIO₄ / tetrahydrofuran / 1 h / 20 °C

8: 82 percent / 2-methyl-2-butene; aq. NaClO₂; KH₂PO₄ / 2-methyl-propan-2-ol / 20 °C

With pyridine; dmap; sodium chlorite; zinc(II) nitrate; sodium periodate; potassium dihydrogenphosphate; 2-methyl-but-2-ene; trimethylsilylazide; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1039/b508855k

upstream raw materials:

(2S,3S,4R,5S)-1-benzyloxycarbonyl-2-formyl-5-methylpyrrolidine-3,4-diol

Downstream raw materials:

(2S,3S,4R,5S)-2-(1H-benzoimidazol-2-yl)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidine

(3aS,4R,6S,6aR)-4-(2-Amino-phenylcarbamoyl)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester